


Start of Something New

by randers1



Category: Chicago PD (TV)
Genre: F/M, Upstead
Language: English
Status: Completed
Published: 2020-07-15
Updated: 2020-07-15
Packaged: 2021-03-05 04:53:44
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,205
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25288618
Author URL: https://archiveofourown.org/users/randers1/pseuds/randers1
Summary: Jay and Hailey reunite after she returns from New York. The story of their first kiss and how upstead comes to fruition.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 24
Kudos: 101





	Start of Something New

**Author's Note:**

> A very long one shot. All characters and elements belong to Dick Wolf.

Hailey stood waiting for the passengers in front of her to get their belongings from the overhead bins and move forward. Even though she was toward the front of the plane it seemed to be taking a very long time. These people were either in absolutely no rush to move their feet or she was very excited to be back home in Chicago. She pursed her lips for a second and gave in to the realization that it was most likely the latter.

When her turn finally came to deplane she nodded her goodbye to the flight attendants and headed to baggage claim. She walked quickly but still took time to look at the large printed posters of the Chicago attractions, smiling at their familiarity.

On the escalator down to the baggage carousels she scanned the people both standing and milling around. She didn't expect to see him here, knew he would be at work, but hoped he'd be free later on this evening. When she’d last spoken to Jay it was last night when she’d confirmed that she was checked in on the morning flight and they talked about making plans for that evening.

On her last night in New York, she had gone out with the task force team for a goodbye round of drinks. Following her exit interviews and file handoffs she’d turned in her badge and left the federal building for good.

“To Chicago!” OA toasted. “Whatever you did to be chosen as our loan out officer, please feel free to do it again!”

Her eyes closed briefly while she chuckled, highly doubting her sergeant would lift his glass to that one. Her bottle clinked against glasses and bottles as the others around the round table agreed with OA.

“You’re welcome back any time,” Isobel had leaned over to stage whisper.

“Thank you,” Hailey looked at her, laughing lightly at everyone’s energy. “It’s a good team. I learned a lot.” She sipped at her beer.

“Listen, just a heads up.” Isobel moved a bit closer so she could speak without the rest of the table hearing. “I spoke to your sergeant earlier, let him know how much of an asset you were to us.” She paused for just a second before continuing. “I wasn’t privy to whatever reason he had for choosing to send you to us, but…I know there was one, there always is. And…whatever that reason was, whatever he wanted you to get out of this, I hope you did.” She nodded once, sitting back.

Hailey was somewhat surprised by the information. The SAC had been friendly enough during her time with the task force but she had never made any attempts to be more than her boss.

“Thank you.” She smiled a bit. “And—yeah. I think I did.” If Hailey was being honest though she didn’t really know that that was true. She saw how the team worked, how they grew frustrated when leads turned cold, when offenders they knew were guilty walked free. She saw how they followed their guidelines, played by the rules, no matter how the cases closed, always swallowing the bitterness and resentment when the cases ended badly, ended wrong. There were times still when Hailey just didn't think she could swallow any more. She saw places she could have acted, ensured that the case turned out right. But her hands were always, frustratingly tied. And she'd have to choke down the anger and aggravation along with the rest of the team.

In the beginning, she’d bristled at the restrictions, something OA had spoken to her about a handful of times when he saw her get jumpy for an outcome that wasn’t coming their way. And he always reminded her that she’d much rather have him rein her in than get Jubal or Castille involved. By her last day she wasn’t quite sure if playing by their rules had simply become second nature or if she’d just gotten better at bending them in her mind. Not that she'd _done_ anything, but was able to clearly see where she could've, and could have done so without detection.

But now she was back. She was home. And that knowledge filled her with a warmth, and a happiness, and a fullness she hadn’t known was missing from her. It felt amazing.

She was still beaming just from having her feet on Chicago’s land when she turned around after picking up her two bags.

“It should be against the law to be as happy as you look right now.” The tall man with the green eyes said as he stood in front of her.

Hailey froze as she saw Jay, heard him speak. Her own words failed as she simply looked at him, her mouth closed, fighting to figure out what kind of smile it wanted to form. Finally, she took a deep and shaky breath, the smile finally fully forming, and breathed out a very simple and happy, ‘Hey.”

“Want to give me that?” He motioned toward the largest bag she had and without waiting, took it from her.

“What are you doing here?” She knew her smile hadn’t faded, couldn’t get rid of it if she tried.

Jay loved her smile. Loved seeing it, loved how her whole face lit up when she wore it. He’d missed it he knew, but seeing it in person again, made something in his chest hitch and tighten. “I heard my partner was back in town. Had to make sure she got a ride…make sure she was ready to rejoin her unit tomorrow.”

She pursed her lips and dipped her head down for a second in a deep nod before looking back up to him. “Your partner is absolutely back in town and cannot _wait_ to be part of intelligence again.”

They stood there, six inches apart, both happy and staring at the other. For Jay, seeing her again erased any doubts or worries that he’d had about awkwardness or tension. There was none of that. And for Hailey, standing in front of Jay again she felt filled with….hope.

It was Jay who spoke when the area became crowded again as a new flight of passengers came to the to pick up their luggage. “Ready to get out of here?”

“I’ll follow you.” She quipped, grinning. He grinned back and they made their way out to his truck.

“Jay?” she was confused as they passed the exit that would have led them to her neighborhood. She turned in her seat to watch the exit sign disappear behind them. “We just passed the exit.”

“Mm hmm” he acknowledged, a small smirk on his lips.

“Where are we going?”

“You’ll see.”

“Jay!” She laughed his name and he loved the sound of it. He hadn’t said hers yet, wanted to wait.

He laughed in return. “Wow, that New York vibe really rubbed off on you. I don’t remember you being so impatient.”

Hailey’s head tilted to the side as she lifted her eyebrows. Her face said _really??_ just as clearly as if she’d spoken.

“Just sit back and relax,” he chided. “We’ll be there soon.”

Hailey sucked her teeth and sat back in her seat.

When he turned the truck on to Lake Shore Drive Hailey grew even more confused. They were nowhere near her house; they were nowhere near any place that she could think of a reason for them to be.

The sight of Lake Michigan drew her eye and she found herself smiling happily out the window. She didn’t see Jay’s glances at her, his own small smile on his face at her reaction to the water.

A few more minutes passed and he pulled off the expressway and parked. Hailey turned to him, perplexed. “Concrete Beach? We’re at Concrete Beach?”

“Come on.” He opened the drivers side door and got out, waiting for her at the front of the truck. When she joined him her hands were in her jacket pockets and she’d pulled her jacket closed to ward off the chill.

Jay was nervous yet somehow calm. He was aware of his nerves but they weren’t running things. He knew what could go wrong right now but he trusted her, and he trusted what he knew and what he felt.

“You ready?”

Hailey’s brow furrowed as they stood there. She’d tried and failed to figure out why they were here. But in the end, she remembered who she was with. It was Jay, and she trusted him. If he’d brought her here there had to be a reason, so she’d roll with it.

She lifted her shoulders in a light shrug and smiled quizzically. “I guess?”

She did freeze though when he pulled his own hand from his jacket pocket and offered it to her. She looked at it then up to him, certain she was confused, that he wasn’t really asking her to take his hand. A few seconds passed and he hadn’t taken it back, instead was still looking at her with an open expression that made her chest rise and fall just a bit faster.

“Yeah?” she questioned quietly.

“If you’re ready.” His face and tone were expectant. The ball was in her court now, and she wondered just when she’d officially signed up to play. As strange as this all was though, somehow it also wasn’t. The fact that she was beside Jay again glossed over absolutely everything else. Tentatively she withdrew her hand from her pocket and put it in his.

He felt the warmth in his hand and gently tightened his grip around it, walking and guiding her away from the truck and down to the sand.

There wasn’t anyone else on this stretch of the beach. They stood a few feet from where the water met the sand, heard the sound of the waves, and Hailey felt her hair twisting all around her. She dropped Jay’s hand to try and smooth it down in a vain attempt to stop the mess. As she did she looked around.It was beautiful here in sight, smell, and sound. But she still wasn’t getting it, didn't know why he'd brought her here.

She turned all the way to Jay, confusion lightly written on her face.

“What is this, Jay?” She pushed hair out of her face again. “What are we doing here?

One of his eyebrows lifted slightly, his expression telling her it should be obvious. She wished it was. “The wind. You said you missed it.” He told her simply. “So here it is.” His voice was so soft and so quiet. Hailey moved her hair from her face once again as she tilted her head and looked at him. Her breath was gone—her heart raced and her chest rose and fell fast but she had no words, couldn’t inhale or exhale for what seemed like forever. She blinked a few times as the memory of her telling him what she missed washed over her. _I miss the wind….and you._. Right now she had both and tears pricked her eyes in response to the thought.

She closed her eyes and turned back toward the water, feeling the wind purposely now, and relishing it.

“Hailey.” He’d said it. Finally. He said it once more. “Hailey?”

Trying to parse out the avalanche of emotions she was under had been company to the wind. But hearing him say her name the way he did, made everything stop. She kept her body toward the lake and turned her head to look at him. She smiled as she tried not to cry. “Can we sit?”

He was quick to answer. “Yeah, sure”

They sat together, hip to hip, in the sand, watching the water.

“Jay, why’d you bring me out here?”

He sighed lightly. “Told you. For the wind.”

Her lips curled up in to a small smile. “This is Chicago. There’s wind everywhere.”

“Yeah, I know,” he agreed with a smile. “Truth is…God, when you were gone, Hailey…when you were gone--- I missed you. A lot….more than I thought I would or could…” He closed his eyes a bit as his brow furrowed, shaking his head. When he opened them he spoke again. “And I just…it was horrible. Hailey. Not having you here.”

Hailey nodded. “I get it.” She was honest with her words, even if he didn’t just _know_ it, he could see it in her eyes. “New York was surreal enough…hard enough… on its own. But not having you there, not seeing you, having a different partner…it was one of the hardest parts.”

He nodded in understanding before speaking quietly, earnestly. "Yeah, but...it was more than. It _is_ more than that." He paused. "I’m gonna hold your hand again,” he warned her.

She smiled at that and huffed out a light puff of laughter, giving her hand over to him.

“Hailey, I thought about you every day.” He admitted relatively easily. “More than I would have if—“ Jay steadied himself with a breath. “if you were _just_ my partner. Somewhere along the way you became more than that. And I feel about you... a way that---that I haven’t felt about anyone in a long…. _long_ time.”

She tilted her head to him, smiling and looking absolutely delighted. He smirked just a bit as he finished. “And I wanted to come clean about that, be upfront about it, before you came back to work. Because Hailey, God, I’m tired of hiding from it.”

He still had more to say but he felt like he’d made a good start. And he hoped that if things went right, he’d have a lot more time to say what he wanted to.

“Jay,” she began, not questioning _him_ per se but most definitely her read of this situation. She’d held on to her feelings for him for so long, had locked them down deep, that for them to be nudged and coaxed, maybe reciprocated, felt like something she might wish for but never really happen.

She looked at him intently, hoping the fear didn’t show on her face, that only hope and happiness did. “Are you saying…”

The feeling of his hand on her cheek stopped her, and she closed her eyes, tilting her head in to it.

“Hey,” she heard him say. “Look at me.”

When she did she found herself looking directly at him. She blinked and tried to control her breathing.

“I think there’s probably a lot we should talk about, but we’ve already missed a lot of time. And right now? I don’t really want to talk.” He used the hand already on her cheek to pull her slightly toward him.

Hailey’s eyes remained opened as she watched him come closer, crossing right into her space. She was aware of _everything_ —the sound of the wind, the feel of it, the water on the shore, the sand under her, his hand on her face, his breath, the scattered freckles across his face and the stubble that grew above it. And then he was right there, his eyes boring into hers, then down at her lips, and the slow, light, electric touch of his lips just grazing hers.

She still hadn’t closed her eyes, realized she hadn’t even kissed him back.

She breathed his name as he watched her, waiting to see her reaction. This time it was she who moved forward, reaching for the back of his head with her hand, holding it there and feeling the soft hairs under her skin. She was still seconds behind him so the look on her face was still serious while a small smile grew on his as he felt the pressure behind him, felt her hand dip down to his neck and gently stroke the skin under his hairline. She pulled him toward her and this time closed her eyes as she kissed him. Not as lightly as he had her but lightly just the same. And a bit longer, savoring the feeling of this newness, the closeness, the pressure of his lips on hers.

When she pulled back she kept her face close to his, her hair still swirling around her. She tried to smooth it down as she smiled. “So this is new.”

“Yeah” he nodded intently. “and late.”

Hailey huffed out a laugh as she pulled back a bit more. “Did you really plan this out?”

Jay too pulled back so that they sat together easily and ran a hand through his hair, noticing it didn’t feel nearly as good as when she’d done it. “Only coming here,” he admitted with a happy smile. “Everything else I definitely thought about though. Wasn’t sure I’d be able—“ His lips flattened.

“I’m glad you did.” She told him with a lifted eyebrow.

“Yeah?” his smirk was back.

She nodded, turning and moving closer again. He saw and did the same, this time reaching for her face with both hands as hers flattened against his chest and bunched his shirt.

They kissed for a while, tentative and soft, every now and then increasing the pressure and probing farther with tongues, hands only wandering short distances.

When Hailey pulled back she was still smiling, though he noticed her sigh.

“You okay?”

“Yeah,” she answered quickly and honestly. “Just---still kind of wrapping my head around this.” She grinned, letting him know it wasn’t a process that she minded. “And…tired.” She chuckled, hating to admit it.

Jay nodded and said nothing, just wrapped an arm around her shoulders and pulled her against him. He looked around, over her head, up at the sky, out to the water and horizon, to the sand around them, absorbing the details of what felt like the start of something new for him, a new chapter of having what he wanted in life.

While Hailey had been gone he’d thrown himself in to the job. Earlier mornings and later nights than normal for him, burying himself in the details of the cases that came their way. It had only been about a week and half of this new normal for him when he overheard the conversations of the rest of the unit talking about weekend plans. They all had them, even if they included purposely doing nothing, and he realized he had none. Zero. He looked around the bullpen and realized that this was all that he had right now. He had his friends here, he knew, his brother, a few buddies over at 51 but there should have been more. When he allowed himself the luxury of dwelling on it he knew that what there should have been normally sat in front of him.

Jay looked forward to their texts and talks while she was gone, was satisfied it was just a matter of time until she came back, but their talks while fun and somewhat flirty he knew, were typically short, and left him wanting and hollow.

That night he’d gone home and called his brother, asked to meet at Molly’s after his shift. Thankfully Will was available and when they met up, Jay started immediately.

Will had just taken his first sip of his beer and choked on it as Jay asked his first question. “You ever regret not getting back together with Natalie?”

“What?!” he choked and wiped at his mouth. “What the hell kind of a question is that?”

“I’m serious, Will. You guys were pretty strong. You ever feel like, maybe she was the one but now…” He’d been fiddling with the bottle as he spoke and now took his own long swig from it.

Will looked at his brother, wondering where this serious line of questioning was coming from. Their normal nights out included dirty jokes, long silences, and the occasional belching contest. Their conversations, when they had them, never had a lot of substance. But tonight he’d roll with it, Will decided, see where it led.

“Umm, I’m not exactly sure how to answer that without looking like a dick.” He smirked.

Jay snorted as Will continued. “I mean, Natalie was great and what we had was amazing but now…Do I miss her? Still think about her? Yeah.” He grimaced at the admission. “But I’m okay without her so I guess…if I’d ever thought she was it for me, I think I’d have been wrong.” He blinked a few times, watching for Jay’s reaction. But nothing changed, his expression remained typically impassive.

Jay was thinking, and when he decided what to say, first furrowed his brow and leaned back a bit, tilting his beer. “I’m not okay.”

Will’s look told him he wasn’t understanding. “I’m alone, Will. For the first time in years. I think if I was alone a few years ago I’d have been okay with that but..” He trailed off with a shrug and a sip of his beer.

Understanding washed over the doctor as he got what Jay was saying and he nodded. “This is about Hailey.”.

It took a good fifteen seconds before Jay responded. “Yeah.”

Will looked at him, never having seen his brother this serious. This wasn’t a brooding Jay or a moody Jay. This was an introspective Jay. Someone who was coming to realizations. “You talk to her?”

“Yeah,” he answered quickly, moving back forward and slightly hunching his shoulders. “Every day but—it’s like it’s not enough.” He sighed. “I miss her.”

Will nodded and tried to choose his words carefully. “Jay, I get it, you guys are close. But do you think..” he swallowed. “that maybe this is just a reaction to her not being here. I mean, not to discount what you’re saying because believe me I _love_ what you’re saying but—it’s the first time you’ve been kind of on your own at work and maybe—“

Jay wasn’t offended, wasn’t defensive; He’d had the same thoughts at first. But now, he just shook his head and answered simply, “No. No, it’s more than that. I think it has been for a while, even before she left. I just—“ He grimaced. “I-- I knew it was there, I think. I just couldn’t see it.”

Will sat back with a huff of satisfaction, a small smirk on his face. “Damn, Jay. When the hell did you grow up?”

A smirk played on Jay’s face as well as he quirked an eyebrow and shook his head, wondering the same thing.

Will continued. “So, I guess the question now is, you have feelings for her, what are you gonna do about it?”

“I don’t know, she’s not even here. And it’s not something I want to text or talk about on the phone.” He glanced at the phone in front of him on the table and gave it a gentle shove.

“She’s coming back though,” Will reminded.

He nodded thoughtfully. “She is.”

There was no hesitation there, Will noted, no insecurity. Just, almost frustrated resignation maybe? That he couldn’t do anything about the feelings he’d discovered. Jay was a man of action and to not be able to act must be killing him.

Will pursed his lips as a crazy thought occurred to him. “You could go to New York.”

Jay chuckled. “Yeah, no,” He lifted the beer to his lips and took a long swig. The idea had crossed his mind one night when thoughts about her and him and what could be and what might be, followed by what might not be, danced around his brain. “I’m not gonna be that guy.”

“What guy?”

“You know, the one that sweeps in and expects her to stop everything and listen to some declaration of love and then what—just leave and I come back here and go back to work? She goes back to work? Lame.”

Will was stuck on the word that Jay had said in the middle of all that. Love? He’d said he missed her, had feelings. But love? Will didn’t know it had gotten that far. The smirk couldn’t be held back. “You love her, huh?”

“What?”

“You said it. You said you love her.”

Jay knit his brow, thinking back. Had he said that? “Wait, well—“ The beer was put down as he rubbed his face with his hands. “Is that what this is? Cuz..yeah,” he spoke the words as the reality hit him. “I do, man. I love her.”

“You still with me?” he heard her ask, felt the small hand on his cheek.

He nodded. “I am. Yeah, sorry. Just thinking.”

She smiled. “Bout what?”

He smiled back. “Taking you home. We have some talking to do, some things I want to tell you.”

She blinked, her face softening. “Yeah?” she breathed. “I may have something I want to tell you too.” She looked content, happy, as she spoke quietly.

He kissed her one more time, watching her through half of it before closing his eyes and sinking deeply in to the feeling.

Afterward, he took her hand again, and pulled her up to him, holding her hand against his chest. “You ready?”

Her bright eyes were clear and full of sincerity as she nodded and answered. “Yeah. Yeah, I am.”


End file.
